5 Lessons from Playwriting and Screenwriting Legend Neil Simon

by Christopher Osterndorf - updated on August 18, 2021

Though he may not be as well-known to modern audiences as peers like Woody Allen and Mel Brooks, Neil Simon is one of America’s preeminent writing legends of stage and screen. The playwright most associated with classic comedies like The Odd Couple has also had a lengthy career in film. In fact, Simon has more combined Oscar and Tony nominations than any other living writer.

While it’s indisputable that Simon’s legacy will ultimately be tied more to his stage work than his film work, movie buffs shouldn’t sleep on Neil Simon. He was working in show business even before he was working on Broadway, and between 27 screenplays, eight made for TV movies, and various credits on television writing staffs, few writers have had such a great impact across multiple mediums. And this isn’t even saying anything of the multiple television and film adaptations which he didn’t write himself but are nevertheless based off his work. 

As is befitting a man who once wrote a play called The Star-Spangled Girl, Simon was born on the 4th of July. In honor of his 91st birthday, here are 5 playwriting and screenwriting lessons from his career which will make anyone a better writer.

1. Always keep writing.

Simon had already been working in television for years on programs like Your Show of Shows by the time his first play, Come Blow Your Horn, premiered in 1961. Because he was so busy with TV work, it took him years to actually complete his final draft of the play. However, Simon didn’t let his day job deter him. Although he describes the process of rewriting as a “monumental effort,” he’s also stated that working on the play over and over again allowed him to find his voice.

Simon says it was “the lack of belief in myself” that made him rewrite Come Blow Your Horn from beginning to end at least 20 times. However, he’s also described this process as “the equivalent of three years of college."

The truth is that there are times as writers where we all doubt ourselves, where we think we’re not good enough. However, these difficult times often end up providing the education we need to make us better. Just because the writing is difficult or doesn’t even seem good is not a reason to quit. If Neil Simon had to rework his first play almost 20 times, it’s a safe bet to say that most of us are going to have to put in a couple drafts before we can break through, too. As the old saying goes, writing is rewriting, and the sooner we accept this often painful fact, the closer we are to success.

Simon went on to become one of the most prolific playwrights in modern history, with new works being premiered all the way up until 2003. It just goes to show that as soon as you can get over that first hump and put the work in, you can go on to do anything.

2. Screenwriting and playwriting - they’re more alike than you think!

As already mentioned, Simon didn’t start out a playwright. Working on Sid Caesar’s Your Show of Shows, he honed his chops alongside some of the greatest comedy writers of the last century, including Carl Reiner, Mel Brooks, and Woody Allen. While Simon wouldn’t have the same kind of careers in television and film as these men, it wasn’t long after the success of his first plays that Hollywood came calling.

Simon chose not to write the screenplay for his first play, Come Blow Your Horn. “I really didn’t have an interest in films then,” Simon recounts. “I was mainly interested in continuing writing for the theater.”  However, he quickly realized that he preferred to adapt the scripts for the movie versions of his work going forward.

Although you can see this disparity in the first few adaptations he did, by the time he got to The Odd Couple in 1968, Simon had better learned how to craft a screenplay that was at least slightly more cinematic than its theatrical counterpart. Eventually, Simon would become comfortable enough with writing for film to pen many original screenplays, including The Heartbreak Kid, Murder by Death, The Cheap Detective, Seems Like Old Times, Max Dugan Returns, The Slugger’s Wife, The Marrying Man, a 1998 sequel to The Odd Couple, and The Goodbye Girl, for which he received an Academy Award nomination. He also worked on the screenplay for 1984’s The Lonely Guy, based on a book by Bruce Jay Friedman.

Again, don’t forget that Neil Simon has written a lot of scripts! The thing is that while his contribution to the American theater may be vaster and more significant, it’s not like some sensibilities don’t translate. Yes, film is expansive and visual where theater is intimate and literary. But good writing is good writing. And who’s better suited to adapt Simon’s work than Simon himself? His career is a testament to the fact that good ideas translate across mediums, and that if you are passionate about what you write, you’re also probably the best person to adapt it. Moreover, his success in creating original material across different forms shows that solid work begets more solid work. Neil Simon is proof that whether it’s TV, film, or theater, the more you do some of it, the better you’re going to be at all of it.

Have a stage play that needs to be produced? Enter the ScreenCraft Stage Play Contest here.

3. Start with the characters.

There are a lot of ways to go about writing a story, but one universal truth is that if your characters aren’t good, your story probably isn’t going to be very good either.

Simon has staked his career on this, again and again, writing characters who are at once extremely flawed and completely relatable. In fact, Simon puts such an emphasis on character, he has stated that he starts by figuring out who the characters in his plays are and then working backward to figure out the plot. He says the one exception to this was the aforementioned Star-Spangled Girl, which was in his words, "the only play I ever wrote where I did not have a clear visual image of the characters in my mind as I sat down at the typewriter." Unsurprisingly, the play was not a hit.

In film, it’s easier to tell plot-driven stories than in theater. Through the use of the camera, editing, and special effects, a movie can create all kinds of machinations to fill out an interesting story around even boring characters. But no one ever wrote a classic play or a classic film where the characters didn’t have some life of their own. As Simon’s plays show us, knowing who your story is about, even before knowing what it is about, is a surefire way to make the audience identify with it.

4. You can stay in your lane while also playing with tone.

Simon’s typically unheroic heroes are not the only trademark of his work. There are also many common themes and motifs which appear throughout his career. Scholars have noted that he frequently focuses on modern life in urban America. His stories also tend to surround working, middle-class people, often daunted by the pressures of capitalism and success in contemporary society. Simon’s protagonists, meanwhile, are usually traditionalists who just want a happy family or a stable love life, despite also being damaged and frequently getting in their own way.

What all of this adds up to is a voice. Simon’s characters, settings, and ideas create a distinct perspective, which is recognizable from story to story throughout his career.

However, just because you found your voice doesn’t mean you have to use that voice to tell only one kind of story. Although mainly considered a comedy writer, Simon has also made a career of playing with tone and style. Whereas something like Barefoot in the Park is a romantic comedy, and something like Rumors is a straight-up farce, a play like The Gingerbread Lady also has elements of tragedy. Or look at his film work. His first Oscar nomination was for The Odd Couple, a definite comedy of manners. But his third was for The Goodbye Girl, which is more of a romantic drama.

Simon himself has warned aspiring comedy writers, "not to try to make it funny. . . try and make it real and then the comedy will come.”  Of his own work, he describes how "I was almost always (with some exceptions) writing a drama that was funny ... I wanted to tell a story about real people."

Simon’s body of work shows that as long as you know your voice, you can write anything. His writing is comedic, frequently filled with funny one-liners and zingers. But he also deals with real issues and situations, and in doing so, stretches the definition of what a traditional “comedy writer” can be.

5. Make it personal.

The final component that makes Simon’s work so compelling is how rooted it is in his own experiences. “Write what you know” is another time-tested cliche, but in Simon’s case, there’s an autobiographical element that adds an additional layer of emotional depth to his work.

Simon has said, "I suppose you could practically trace my life through my plays," and the parallels are not hard to spot. Often, Simon’s stories are about Jewish, middle-class New Yorkers, like himself. They also often revolve around unhappy childhoods and marriages, both of which Simon has dealt with in his lifetime. Simon’s Brighton Beach trilogy, also known as the “BB” trilogy or the Eugene trilogy, including the plays Brighton Beach, Biloxi Blues, and Broadway Bound, took this to a new level. Each play traces the life of Eugene Morris Jerome, from his teenage years to young adulthood. The character is a stand-in for Simon himself, and the trilogy tells a version of Simon’s own coming of age story.

Simon’s play, Lost in Yonkers, also relied heavily on his own experiences growing up, and for that one, he was awarded the Pulitzer Prize. But even Simon’s plays which are less directly about his life tend to be autobiographical in some way. More than anything, they reflect the outlook that his experiences have given him on the world.

This is the real takeaway for aspiring writers. Whether your work is more or less autobiographical, it should at least say something about who you are. An audience can always feel the emotion behind a story that’s more personal, which is why more personal stories so often end up being the better ones.

Chris Osterndorf is a freelance writer from Milwaukee who studied cinema at DePaul University in Chicago. When he's not watching movies, he's writing them or writing about them. He's especially partial to romantic comedies and crime films. He currently lives in Los Angeles.

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